Legal Innovation

Subscribe to Legal Innovation via RSS

This week on The Geek in Review, we talk with Ryan McClead of Sente Advisors about his new book on AI agents, written in collaboration with Claude. McClead explains how a short best practices guide grew into a full book after his work with Claude Cowork revealed something larger than tool tips or prompt advice. The result is part field guide, part warning label, and part first-person report from the edge of agentic AI adoption in legal work.

Download it as a PDF for free here.
Or purchase a printed copy here.

McClead’s process flips the traditional writing model. Instead of staring at a blank page, he asked Claude to generate an outline and draft, then spent weeks shaping, cutting, challenging, and refining the work. The book became a study in collaboration, with McClead serving as author, editor, supervisor, and occasional bouncer when the AI wandered too far from the point. His description of training Claude toward his voice, “more Anthony Bourdain and less Bobby Flay,” gives the episode one of its best lines and one of its most useful lessons.

A central idea from the conversation is “executable knowledge.” McClead argues knowledge management teams need to think beyond content meant for humans to find and read. The next stage is knowledge structured, so AI agents understand when to use it, how to apply it, and how to turn it into repeatable workflows. For law firms, this raises practical questions around scale, security, permissions, data quality, and governance. It also creates a new role for KM and innovation teams as builders of reusable legal intelligence.

The discussion also moves past prompt engineering as the main AI skill. McClead describes a shift from prompting to delegation, where users set goals, provide context, invite clarifying questions, and supervise the work product. The human role does not shrink in this model. It becomes more focused on judgment, direction, taste, and knowing when to take the work away from the AI before endless iteration turns progress into mush.

By the end of the episode, McClead frames AI agents less as replacements and more as strange new colleagues whose usefulness depends on the expertise of the person directing them. Good lawyers, KM professionals, and innovation leaders get faster and more effective. Poor processes get accelerated too, which is where the danger sits. For legal organizations, the message is clear: start small, learn the tool, build guardrails, and prepare for a future where clients ask not only for legal answers, but for legal workflows they can run.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Ryan McClead on Writing With Claude and What AI Agents Mean for Legal Work

This week on The Geek in Review, we talk with Alex Su and Andy Chagui of Latitude about the shifting economics of law firm talent, the rise of flexible legal staffing, and the pressure AI is placing on traditional leverage models. Su, known across legal circles for his sharp commentary and creative legal industry videos, brings his background as a former Sullivan & Cromwell litigator and federal clerk to his current work leading revenue strategy at Latitude. Chagui adds the perspective of a former Carlton Fields shareholder who spent 15 years handling high-stakes federal litigation before moving into the new law space. Together, they offer a practical view of where law firm staffing is headed as clients, firms, and legal departments all face rising expectations around speed, value, and technology adoption.

Latitude’s model centers on high-end, flexible legal talent, experienced attorneys with Big Law or in-house backgrounds who step into law firms and corporate legal departments for specific engagements. Chagui explains that these lawyers often support overflow work, leave coverage, secondment requests, internal projects, and interim needs across practices ranging from litigation to corporate, labor, and employment. Su adds that staffing itself is not new, yet Latitude focuses on a segment of talent that traditional hiring models often miss, experienced attorneys with strong credentials who prefer engagement-based work over the standard full-time track.

The conversation turns quickly to why this model is gaining traction now. Remote work, post-COVID hiring shifts, and the growing acceptance of distributed teams have made it easier for firms to bring in experienced attorneys without requiring long-term headcount commitments. Chagui notes that many Latitude attorneys have 10 or more years of experience, meaning they often need less supervision than junior lawyers and move quickly into productive work. This matters as firms face inconsistent demand, intense competition for talent, and hesitation around layoffs, which in law firms often signal weakness rather than discipline.

AI adds another layer to the staffing problem. Firms have invested in tools such as Harvey, CoCounsel, and other specialized platforms, yet many knowledge management and innovation teams lack enough subject matter experts to train users, review outputs, build use cases, and handle quality control. Chagui describes Latitude lawyers helping firms train internal AI tools, review AI-generated work, and support practice-specific rollout efforts. Su points out that while some firms offer associates credit for AI training or innovation work, associates under billable hour pressure often choose client work first. Flexible talent gives firms another way to support AI adoption without asking already-stretched associates to carry the full load.

Su also frames flexible talent as a new form of leverage. Clients still trust senior partners and often accept premium rates for high-value judgment, but they are increasingly skeptical of paying top-tier rates for junior-level work. In that middle layer of legal work, AI, technology, and experienced flexible attorneys give firms more options. Su calls this “outsourced leverage,” a way to support the partner-client relationship while rethinking who performs the work underneath. The discussion also highlights a career-path shift for attorneys who prefer specialized, project-based work, especially in areas like knowledge management, AI implementation, and innovation support.

Looking ahead, both guests see uncertainty as the defining feature of the next phase of legal services. Chagui expects the traditional model to keep changing as firms and legal departments seek more flexible options. Su predicts continued upheaval around staffing, AI capabilities, and outside counsel relationships, especially as foundational AI models move further into in-house legal workflows such as NDA review, contract review, and eventually parts of diligence. Yet Su also offers a reminder for law firm leaders: premium legal judgment still has value. The rates for top partners are unlikely to fall simply because AI improves. The pressure will land instead on how firms structure the work beneath them.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Alex Su and Andy Chagui on Flexible Legal Talent, AI Pressure, and the Future of Law Firm Leverage

This week on The Geek in Review, we talk with Lennie Nuara, co-founder of Flatiron Law Group, about what it means to build a talent-first, AI-powered legal practice. Nuara brings a rare mix of lawyer, technologist, operator, and systems thinker to the conversation, drawing from decades of experience using technology to improve legal work, from early portable computers and databases to today’s generative AI tools.

Nuara explains why he resists the phrase “AI-first” in legal practice. For him, legal work begins with talent, judgment, and expertise. AI enters as a force multiplier, not the driver. At Flatiron, the firm’s model was already built around flat fees, lean staffing, process discipline, and structured data before generative AI entered the picture. AI now adds more horsepower to a system already designed to reduce waste, repeat touches, and unclear workflows.

Much of the discussion focuses on M&A due diligence, where Flatiron rethinks the deal life cycle from intake through closing. Instead of throwing documents into a massive repository and hoping AI sorts it out, Nuara describes breaking work into smaller pieces: diligence questions, responses, documents, clauses, topics, closing checklists, and reports. That structure lets lawyers use AI for deduplication, extraction, clause comparison, first-pass drafting, and issue spotting while keeping human judgment between higher-risk steps.

Nuara also warns against getting seduced by polished AI output. He describes generative AI as persuasive, fluent, and sometimes dangerously average. The bigger risk, in his view, is less hallucination and more “model monoculture,” where legal drafting drifts toward sameness because models train from overlapping bodies of public material. In complex private transactions, average language is often the wrong answer. Lawyers still need to understand leverage, client priorities, risk allocation, and where to push beyond market terms.

The episode closes with a look at pricing, training, and the future structure of law firms. Nuara argues that AI will pressure the billable hour, change junior lawyer training, and force firms to rethink the traditional pyramid. He also raises a practical concern from the early Westlaw and Lexis days: the cost of the tool matters. Flatiron tracks AI usage down to the clause level, treating tokens as part of matter economics. For legal professionals watching AI reshape transactions, this conversation offers a grounded reminder: better tools matter, but better process and better judgment still decide the outcome.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Flatiron Law Group’s Lennie Nuara on Talent-First AI, M&A Workflows, and the Future of Legal Practice

This week on The Geek in Review, we talk with Greg Mazares Sr., CEO of Purpose Legal, about what it takes to lead through one of the most important transition periods in legal services. Drawing on decades of experience across business, litigation support, and e-discovery, Mazares brings a steady, practical view to a market flooded with AI claims and rapid change. His message is clear from the start. The legal industry has faced major shifts before, from paper banker boxes to digital workflows, and this moment is another chapter in that longer story. Rather than treating AI as a threat, he sees it as a tool for adaptation, growth, and smarter client service.

A central theme in the conversation is Mazares’ belief that AI works best when paired with people and disciplined process. He argues that the future does not belong to technology alone, but to organizations that know how to combine tools, talent, and operational rigor. That philosophy sits behind Purpose Legal’s acquisition of Hire Counsel and its broader push to reunite technology and staffing under one roof. In Mazares’ view, clients do not simply want software. They want experienced professionals who know how to apply AI in defensible, repeatable ways that improve outcomes without sacrificing judgment.

The discussion also highlights Purpose Legal’s new offerings, including Purpose Xi and Case Optics, which aim to deliver early case insights in days rather than weeks. What makes Mazares’ framing stand out is his insistence that speed alone is not the point. Faster results matter only when paired with expert validation, tested workflows, and credible guardrails. He describes a legal market where clients once assumed AI would let them bring everything in-house, but now increasingly value outside experts who bring both technological fluency and hard-earned experience. That shift, he suggests, is raising the level of service providers from operational support teams to strategic partners embedded more deeply in legal work.

Greg and Marlene also press Mazares on data security, client trust, and the cultural pressures that come with rapid growth. Here again, his answers return to discipline and execution. He points to major investments in cloud security, around-the-clock protection teams, and tighter controls over on-site review environments. He also argues that many of the greatest risks still come from human behavior, which makes vetting, supervision, and protocol design as important as any technical control. On culture, Mazares emphasizes recognition, communication, and adaptability as the backbone of a company that wants to grow without losing its identity. For him, scaling a business is not only about revenue. It is about building a place where people feel seen, trusted, and prepared for change.

The episode closes on a thoughtful look at the next few years for litigation, junior associates, and the billable hour. Mazares predicts that junior lawyers will not disappear, but their role will shift toward becoming guides in the use of AI, both inside firms and in conversations with clients. As routine work becomes more compressed, he expects associates to provide higher-value service in fewer hours, with stronger technical fluency and a more consultative posture. It is a fitting end to an episode grounded in realism rather than hype. Mazares does not present AI as magic, and he does not dismiss its significance either. Instead, he offers a view of the future shaped by adaptability, experience, and the belief that in legal services, the winning formula still comes down to people, process, and sound judgment.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Greg Mazares Sr. on AI, E-Discovery, and the Future of Human-Led Legal Services

The latest episode of The Geek in Review finds Greg Lambert and Marlene Gebauer back from Dallas with a sharp, grounded recap of the Texas Trailblazers conference, an event that stayed close to the daily realities of legal work instead of drifting into glossy predictions. Their conversation centers on a legal industry trying to sort out what AI means right now, in billing, workflow, training, pricing, governance, and client expectations. What stands out most is the hosts’ focus on the practical tension between what the tools are capable of and what law firms and legal departments are structurally ready to absorb.

A major thread in the discussion is the risk of what one speaker called “cognitive surrender,” the habit of trusting AI output too quickly and handing off too much human judgment in the process. Greg and Marlene treat this as less of a software issue and more of a workflow and education issue. The point is not whether AI produces polished work. The point is whether organizations are building systems where review, judgment, and accountability still sit with people. Their conversation ties this concern to legal practice, education, and even K-12 learning, showing how widespread the temptation has become to accept fluent output without enough friction or scrutiny.

The episode also takes a hard look at the pressure AI is putting on the billable hour. Marlene frames the issue well when she notes that AI does not kill the billable hour so much as expose its weaknesses. Across the conference, the hosts heard repeated concern about the mismatch between efficiency gains and the financial structures law firms still rely on. If AI reduces the time needed for many tasks, then firms, associates, pricing teams, and clients all have new incentives to sort through. Greg and Marlene highlight the awkward moment the industry is in, where firms want to talk about value while clients are also eyeing the chance to pay less for faster work. The result is a growing need for honest conversations about pricing, outcomes, and what legal value should mean when time is no longer the cleanest measure.

What gives the episode its energy is the number of concrete examples pulled from the conference. The hosts discuss lower-cost multi-state surveys, large-scale analysis of rights-of-way documents, and internal workflow improvements built with existing tools like SharePoint and Copilot on little or no budget. These stories show AI not as abstract promise, but as a way to get work done that used to be too expensive, too tedious, or too slow to tackle at all. At the same time, Greg and Marlene stay skeptical in the right places, especially when the conversation turns to legal research, citation accuracy, and the idea that technology vendors have somehow solved problems that law librarians and researchers know are stubbornly difficult.

By the end of the episode, the biggest takeaway is not that the legal industry has a clear answer, but that waiting for certainty is no longer a serious option. Greg and Marlene come away from Texas Trailblazers with a sense that real progress is happening through testing, discussion, and repeated adjustment, not through perfect plans. Their recap captures an industry in transition, one where law firms, legal ops teams, vendors, and clients are all feeling the strain between old business models and new technical possibilities. The message is simple and urgent: start the conversations now, use the tools now, and get honest about what must change before the gap between what is possible and what is workable gets even wider.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠
Transcript:

Continue Reading Texas Trailblazers and the Hard Truth About AI in Legal Work

Anastasia Boyko joins us this week for a wide-angle conversation about AI adoption, leadership, and the uncomfortable truth behind “we are watching what peer firms do.” A Yale-trained tax lawyer with experience spanning Axiom, legal education, and innovation leadership, Boyko argues that precedent-driven instincts are turning into a liability when the underlying rules of the market are shifting in real time.

The episode opens with lessons from the Women + AI 2.0 Summit at Vanderbilt and the “AI competence penalty” narrative. Boyko’s central principle for law firm leaders is simple, stop copying the competition and start operating with intention. Strategic planning matters more than tool shopping, especially when uncertainty makes leaders freeze, over-index on fear, or chase noise instead of outcomes.

From there, the conversation sharpens into client reality. Boyko shares what she is hearing from in-house leaders, and it is not comforting for firms. Legal departments are working to reduce dependence on outside counsel, business partners inside companies often accept “good enough,” and the models keep improving. The risk is not losing to a peer firm; it is losing the client relationship because the work stops feeling necessary.

A major theme is talent and the apprenticeship gap. Boyko argues firms underinvest in people, even as they spend aggressively on software stacks. AI can help junior lawyers with coaching and confidence, but it does not replace mentorship, judgment-building, or context. The skills that matter now include client advisory, operational thinking, critical judgment, and the ability to solve problems across a complex system, not only perform discrete tasks in a vacuum.

The episode closes on legal education and the future value of the JD. Boyko urges students to be selfish about learning AI, especially when faculty guidance comes from avoidance or philosophy rather than experimentation. Looking ahead, she predicts the JD’s value shifts upward, away from rote production and toward proactive advisory work, relationships, anticipatory counsel, and wisdom-driven judgment. In other words, fewer fire drills, more looking around corners.

Links:

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Anastasia Boyko on Advisor Mode, Training Lawyers for the Post-Pyramid Firm

Ray Brescia joins The Geek in Review this week to unpack a role with peak academia vibes, Associate Dean for Research and Intellectual Life at Albany Law School. Greg frames the title as “Chief Curator of Smart People Ideas,” and Ray embraces a “player-coach” approach, coaching faculty scholarship, unblocking stalled projects, and connecting peers across disciplines. The throughline is community, research momentum, and a practical view of how ideas move from draft to impact.

The conversation then pivots to the core thesis of Ray’s book, Lawyer 3.0. Ray maps the legal profession across three eras: Lawyer 1.0 as a low-barrier “amorphous bar,” Lawyer 2.0 as the institutional buildout of law schools, bar exams, ethics codes, and modern law firms, and Lawyer 3.0 as the next inflection point driven by technology. Ray ties prior shifts to urbanization, immigration, and industrial-scale commerce, then parallels those forces with today’s generative AI and analytics reshaping research, drafting, discovery, and service delivery.

Ray retells the famous milkshake study, then translates the idea into legal services: clients are not shopping for “a lawyer,” clients are shopping for problem resolution. This reframing pushes law firms to examine intake, scoping, and service design through the lens of client outcomes, business problems, and life problems, not internal practice labels. The milkshake becomes a metaphor for product-market fit in law, with fewer crumbs on the steering wheel.

Ray contrasts “bespoke services” with productized pathways, including a Model T style offering that meets most client needs at lower cost, plus higher-cost custom work when risk or complexity demands. Ray highlights expert-system style workflows such as Citizenshipworks, describing a TurboTax-like experience for straightforward matters, with “red flags” triggering referral to a lawyer. The same logic extends to limited scope representation and “lawyer for the day” programs in high-volume courts, where informed consent, reasonable scope, and “first, do no harm” reduce the chance of clients feeling abandoned midstream.

The final stretch tackles law firm AI adoption, hallucination risk, and professional responsibility. Ray stresses minimum competence: verify cases, verify quotations, verify sources, and treat generative outputs as drafts or starting points, not final work product. The panel discusses guardrails, education, and workflow design for large firms, plus the rising reality of clients arriving with AI-generated “research.” Ray’s crystal ball points toward more commoditized legal services at scale, a latent market of underserved people, and stronger interdisciplinary collaboration between lawyers and technologists so legal education aligns with Lawyer 3.0 realities.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript

Continue Reading Lawyer 3.0 and the Milkshake Test: Ray Brescia on Legal AI, Client Value, and the Next Wave of Lawyering

The Geek in Review closes 2025 with Greg Lambert and Marlene Gebauer welcoming back Sarah Glassmeyer and Niki Black for round two of the annual scorecard, equal parts receipts, reality check, and forward look into 2026. The conversation opens with a heartfelt remembrance of Kim Stein, a beloved KM community builder whose generosity showed up in conference dinners, happy hours, and day to day support across vendors and firms. With Kim’s spirit in mind, the panel steps into the year-end ritual: name the surprises, own the misses, and offer a few grounded bets for what comes next.

Last year’s thesis predicted a shift from novelty to utility, yet 2025 felt closer to a rolling hype loop. Glassmeyer frames generative AI as a multi-purpose knife dropped on every desk at once, which left many teams unsure where to start, even when budgets already committed. Black brings the data lens: general-purpose gen AI use surged among lawyers, especially solos and small firms, while law firm adoption rose fast compared with earlier waves such as cloud computing, which crawled for years before pandemic pressure moved the needle. The group also flags a new social dynamic, status-driven tool chasing, plus a quiet trend toward business-tier ChatGPT, Gemini, and Claude as practical options for many matters when price tags for legal-only platforms sit out of reach for smaller shops.

Hallucinations stay on the agenda, with the panel resisting both extremes: doom posts and fan club hype. Glassmeyer recounts a founder’s quip, “hallucinations are a feature, not a bug,” then pivots to an older lesson from KeyCite and Shepard’s training: verification never goes away, and lawyers always owed diligence, even before LLMs. Black adds a cautionary tale from recent sanctions, where a lawyer ran the same research through a stack of tools, creating a telephone effect and a document nobody fully controlled. Lambert notes a bright spot from the past six months: legal research outputs improved as vendors paired vector retrieval with legal hierarchy data, including court relationships and citation treatment, reducing off-target answers even while perfection stays out of reach.

From there, the conversation turns to mashups across the market. Clio’s acquisition of vLex becomes a headline example, raising questions about platform ecosystems, pricing power, and whether law drifts toward an Apple versus Android split. Black predicts integration work across billing, practice management, and research will matter as much as M&A, with general tech giants looming behind the scenes. Glassmeyer cheers broader access for smaller firms, while still warning about consolidation scars from legal publishing history and the risk of feature decay once startups enter corporate layers. The panel lands on a simple preference: interoperability, standards, and clean APIs beat a future where a handful of owners dictate terms.

On governance, Black rejects surveillance fantasies and argues for damage control, strong training, and safe experimentation spaces, since shadow usage already happens on personal devices. Gebauer pushes for clearer value stories, and the guests agree early ROI shows up first in back office workflows, with longer-run upside tied to pricing models, AFAs, and buyer pushback on inflated hours. For staying oriented amid fractured social channels, the crew trades resources: AI Law Librarians, Legal Tech Week, Carolyn Elefant’s how-to posts, Moonshots, Nate B. Jones, plus Ed Zitron’s newsletter for a wider business lens. The crystal ball segment closes with a shared unease around AI finance, a likely shakeout among thinly funded tools, and a reminder to keep the human network strong as 2026 arrives.

Sarah Glassmeyer

Niki Black

Marlene Gebauer

Greg Lambert

Transcript

Continue Reading Receipts, RAG, and Reboots: Legal Tech’s 2025 Year-End Scorecard with Niki Black and Sarah Glassmeyer

For decades, “the record” has meant one thing: a text transcript built by skilled stenographers, trusted by courts, and treated as the backbone of due process. In this episode of The Geek in Review, Marlene Gebauer and Greg Lambert sit down with JP Son, Verbit’s Chief Legal Officer, and Matan Barak, Head of Legal Product, to talk about what happens when a labor shortage, rising demand, and better speech technology collide. Verbit has been in legal work since day one, supporting court reporting agencies behind the scenes, but their latest push aims to modernize the full arc of proceedings, from depositions through courtroom workflows, with faster turnaround and more usable outputs.

A core tension sits at the center of the conversation: innovation versus legitimacy. Marlene presses on whether digital records carry the same defensibility as stenographic ones, and JP frames Verbit’s posture as support, not replacement. Verbit is not a court reporting agency; their angle is tooling that helps certified professionals and agencies produce better outcomes, including real-time workflows that once required heavy manual effort. The result is less “robots replace reporters” and more “reporters with better gear,” which feels like the only way this transition avoids an industry food fight in every courthouse hallway.

From there, the discussion shifts into the practical, lawyer-facing side: LegalVisor as a “virtual second chair.” JP describes it as distinct from the official transcript, a real-time layer built to surface insights, track progress, and support strategy while the deposition is happening. Matan adds the design story, discovery work, shadowing, and interviews to build for what second chairs are already doing, hunting inconsistencies, chasing exhibits, and keeping the outline on track. A key theme: the transcript is not going away, because lawyers still rely on it for clients, remote teammates, and quick backtracking, but the value climbs when the transcript turns into a live workspace with search, references, and outline coverage in front of you while testimony unfolds.

Accuracy and trust show up as recurring guardrails. Greg pokes at the “99 percent accurate” claims floating around the market, and Matan makes the point every litigator appreciates, the missing one percent contains the word that flips meaning. Verbit’s “human in the loop” posture and its Captivate approach focus on pushing accuracy toward the level legal settings require, including case-specific preparation by extracting names and terms from documents to tune recognition in context. The episode also tackles confidentiality head-on, with JP drawing a hard line: Verbit does not use client data to train generative models, and they keep business pipelines separate across verticals.

Finally, the crystal ball question lands where courts love to resist, changing the definition of “the record.” Marlene asks whether the future record becomes searchable, AI-tagged video rather than text-first transcripts. JP says not soon, pointing to centuries of text-based infrastructure and the slow grind of institutional acceptance. Matan calls the shift inevitable, arriving in pieces, feature by feature, so the system evolves without pretending it is swapping the engine mid-flight. Along the way, there are glimpses of what comes next, including experiments borrowing media tech, such as visual description to interpret behavior cues in video. The big takeaway feels simple: the record stays sacred, but the work around it no longer needs to stay stuck.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading The Record, Rewired: Verbit and the Next Era of Court Reporting – JP Son and Matan Barak

In this episode of The Geek in Review, we sit down with Narrative founder John Tertan to talk about law firm pricing, messy data, and why substance matters more than shiny tools. We pick up from our first meeting at the Houston Legal Innovators event, where John had the pricing and KM crowd buzzing, and ask what he is hearing from those teams as they look toward 2026. John explains how Narrative focuses on “agentifying” business-of-law work, starting with pricing and analytics, so firms stop guessing and start grounding decisions in better data. The goal is simple, improve decisions for pricing teams, finance, marketing, and partners who want to win work that also makes financial sense.

John walks through the pain points that drive firms to seek out Narrative, from low realization and high write-offs to tedious non-billable work and a lack of trust in the data behind pitches and budgets. Many firms track key metrics in scattered spreadsheets, checked once in a while rather than used as a daily guide for strategy. Narrative steps into that gap by improving the accuracy of historical matter data, identifying the right reference matters for new proposals, and supporting alternative fee structures. John explains how this foundation supports better scoping, more confident pricing conversations, and far stronger alignment between firm goals and client expectations.

We also dive into John’s founder journey, which runs from Freshfields associate to innovation work, then through venture-backed tech in other sectors before returning to legal. That mix of big law, startup experience, and prior success with HeyGo shapes how he builds Narrative. John talks about serving “mature customers” who expect more than a slick interface, they expect real understanding of their business, their politics, and their constraints. Relationships sit at the center of his approach, not only with clients and prospects, but also with advisors, former firm leaders, and legal tech veterans who guide both product and go-to-market strategy.

The name “Narrative” is no accident, and John explains why time entry narratives sit at the heart of his product. Those lines of text describe what lawyers did, for whom, and why, yet they often sit underused in billing systems. Narrative improves and structures that data, then uses it to highlight scope, track what remains in or out of scope, and surface early warnings when matters drift away from the original plan. John talks through the life cycle, from selecting comparable matters, through modeling AFAs and scenarios, to monitoring work in progress and feeding lessons back into future pricing efforts. Along the way, better transparency supports stronger trust between partners and clients.

We close by asking John to look ahead. He shares his view on how firms will move toward more sophisticated pricing models and better measurement, while the billable hour continues to evolve rather than vanish overnight. Stronger baselines, cleaner matter histories, and better tracking create room for fee caps, success components, and other structures that clients want to sell internally. John also shares how he stays informed through alerts, networks, and a new chief of staff who helps turn those insights into resources for pricing and finance professionals. For listeners who want to learn more or follow Narrative’s work, John points them to narrativehq.com and invites outreach from anyone wrestling with data, pricing, or margin questions inside their own firm.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading From Bad Data to Better Deals: John Tertan on Narrative, Pricing, and Law Firm Relationships